Abstract
A procedure has been developed for the concise synthesis of hexahydro-1H-isoindole derivatives starting from phenacyl bromides. The approach employs a sequence involving an initial indium-mediated allenylation reaction of an arylacyl bromide with propargyl bromide. This process is followed by FeBr3-mediated SN2′-type substitution reaction of the formed homoallenic bromohydrin to produce a 2,5-dibromo-4-aryl-1,3-pentadiene, which then is subjected to a sequential, one-pot N-alkylation reaction with N-allyl-N-(p-tosyl)amine and a highly diastereoselective intramolecular Diels-Alder reaction of the formed ene-diene to generate the target hexahydro-1H-isoindole.
Original language | English |
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Pages (from-to) | 2462-2466 |
Number of pages | 5 |
Journal | Journal of Organic Chemistry |
Volume | 80 |
Issue number | 4 |
DOIs | |
Publication status | Published - 2015 Feb 20 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry